5-Bromo-2-(4-fluoro­phen­yl)-3-phenyl­sulfinyl-1-benzofuran

Pil Ja Seo; Hong Dae Choi; Byeng Wha Son; Uk Lee

doi:10.1107/S1600536811032387

. 2011 Aug 17;67(Pt 9):o2346. doi: 10.1107/S1600536811032387

5-Bromo-2-(4-fluorophenyl)-3-phenylsulfinyl-1-benzofuran

Pil Ja Seo ^a, Hong Dae Choi ^a, Byeng Wha Son ^b, Uk Lee ^b,^*

PMCID: PMC3200819 PMID: 22064889

Abstract

In the title compound, C₂₀H₁₂BrFO₂S, the 4-fluorophenyl ring makes a dihedral angle of 2.63 (6)° with the mean plane of the benzofuran fragment. The dihedral angle between the phenyl ring and the mean plane of the benzofuran fragment is 84.60 (6)°. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds, and slipped π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.719 (3) Å, interplanar distance = 3.000 (3) Å and slippage = 1.520 (3) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of related 5-halo-2-(4-halophenyl)-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C₂₀H₁₂BrFO₂S
M _r = 415.27
Triclinic,
a = 8.0090 (2) Å
b = 9.8607 (3) Å
c = 11.7209 (3) Å
α = 70.471 (2)°
β = 83.171 (2)°
γ = 69.583 (2)°
V = 817.59 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.66 mm⁻¹
T = 173 K
0.29 × 0.19 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.513, T _max = 0.649
15330 measured reflections
4102 independent reflections
3428 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.082
S = 1.02
4102 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032387/zl2399sup1.cif

e-67-o2346-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032387/zl2399Isup2.hkl

e-67-o2346-Isup2.hkl^{(201KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811032387/zl2399Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.58	3.460 (2)	154
C19—H19⋯O2ⁱⁱ	0.95	2.55	3.413 (3)	150

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Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

Many compounds containing a benzofuran ring system have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 5-halo-2-(4-halophenyl)-3-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2010, 2011), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.008 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofuran fragment is 2.63 (6)°, and the dihedral angle between the phenyl ring and the mean plane of the benzofuran fragment is 84.60 (6)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a 4-fluorophenyl H atom and the O atom of the sulfinyl group (Table 1; C13—H13···O2ⁱ), and the second one between a phenyl H atom and the O atom of the sulfinyl group (Table 1; C19—H19···O2ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by weak slipped π–π interactions between the benzene rings of adjacent molecules, with Cg···Cgⁱⁱⁱ distance of 3.719 (3) Å and an interplanar distance of 3.000 (3) Å resulting in a slippage of 1.520 (3) Å (Cg is the centroids of the C2–C7 benzene ring).

Experimental

77% 3-chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-bromo-2-(4-fluorophenyl)-3-phenylsulfanyl-1-benzofuran (319 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 67%, m.p. 473–474 K; Rf = 0.70 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.